Cayman Islands Vacation Rentals - Caribbean Holiday Rentals in Cayman Islands

  Holiday Rentals in Cayman Islands
   World Holiday Homes 
      Caribbean Holiday Homes 
            Cayman Islands (35 properties)

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Cayman Brac Holiday Homes   (0 properties)  
Grand Cayman Holiday Homes   (33 properties)  
Breakers   North West Point   Rum Point/Cayman Kai   Seven Mile Beach  
East End   Northside  
Little Cayman Holiday Homes   (1 properties)  

Use the filters below to narrow down the 35 Condominiums and rentals we have in Cayman Islands

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Holiday Condominium rental in Rum Point/Cayman Kai, Grand Cayman
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Holiday Condominium rental in Rum Point/Cayman Kai, Grand Cayman

Cayman Breeze Oceanfront in Cayman Kai

Cayman Breeze is a new luxury 2/2 direct ocean and beachfront condominium located in beautiful Cayman Kai.

bedrooms  2    bathrooms2
sleeps 4 - 6

$1750 - $2200
Per Week
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Not Near A Golf Course Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation rental Villa in Northside
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Vacation rental Villa in Northside

6BR Twin Palms in Rum Point

6BR Large Beach House in Rum Point

bedrooms  6    bathrooms4
sleeps 12

$4950 - $6450
Per Week
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Condominium in Seven Mile Beach, Grand Cayman
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Holiday Condominium in Seven Mile Beach, Grand Cayman

Simply Cayman

Ocean front on Seven Mile Beach. Walking distance to town.

bedrooms  2    bathrooms2
sleeps 8

$1800 - $2700
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Villa in Rum Point/Cayman Kai, Grand Cayman
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Villa in Rum Point/Cayman Kai, Grand Cayman

4BR "Rainbows End"-Perfect Beach

4BR Oceanfront villa with perfect white sand beach--walk to Rum Point Club

bedrooms  4    bathrooms4
sleeps 8 - 12

$5585 - $6950
Per Week
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Rental Condominium in Rum Point/Cayman Kai
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Rental Condominium in Rum Point/Cayman Kai

CaymanOnTheBeach

Kaibo ground floor condo on shore of Cayman Kai, the exclusive rum point area.17 feet of glass door face water

bedrooms  2    bathrooms2
sleeps 6

$1400 - $1900
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Holiday House in Rum Point/Cayman Kai, Grand Cayman
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Holiday House in Rum Point/Cayman Kai, Grand Cayman

Island Houses of Cayman Kai

Cayman Kai Vacations specializing in offering "The Island Houses of Cayman Kai" Vacation Rentals

bedrooms  2    bathrooms2
sleeps 6 - 8

$1925 - $2625
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
1 bedroom Villa in Rum Point/Cayman Kai
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1 bedroom Villa in Rum Point/Cayman Kai

Villa Azure Rum Point/Cayman Kai

Baby Boomers and Baby Makers!

bedrooms  1    bathrooms2
sleeps 2 - 4

€315 - €415
Per Day
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
7 bedroom Guest House for rent in Breakers
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7 bedroom Guest House for rent in Breakers

Tropical Breeze and Royal Palm Cottages

Cayman Seaside Cottages are ideal charming Cayman vacation cottages for the budget minded traveler. .

bedrooms  7    bathrooms7
sleeps 14 - 16

$85 - $215
Per Day
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Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Villa for rent in Northside
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Villa for rent in Northside

northern lights beachfront condos

northern lights is a small luxury condo complex on the quiet northcoast of grand cayman

bedrooms  2    bathrooms3
sleeps 4

$200 - $300
Per Day
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Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation rental Villa in Northside
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Vacation rental Villa in Northside

Beachplum

Luxury Villa with Private Beach and Fresh Water Pool

bedrooms  4    bathrooms5
sleeps 8

$4500 - $5950
Per Week
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Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Villa in Northside, Grand Cayman
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Holiday Villa in Northside, Grand Cayman

4BR "Sand Castle" with Pool

4BR Oceanfront villa with pool in Old Man Bay

bedrooms  4    bathrooms5
sleeps 8 - 10

$4950 - $7450
Per Week
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday House in Seven Mile Beach, Grand Cayman
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Holiday House in Seven Mile Beach, Grand Cayman

Jeff's Grand Cayman Private Homes

Private 2 bdrm "home away from home", within 2 blocks of best snorkeling on all of SMB!
"Cayman's Best Value!"

bedrooms  2    bathrooms2
sleeps 6

$895 - $1095
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Villa for rent in Rum Point/Cayman Kai
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Villa for rent in Rum Point/Cayman Kai

4BR "Gypsy" Oceanfront in Rum Point

4BR Luxury Oceanfront Gypsy with pool

bedrooms  4    bathrooms4
sleeps 8 - 9

$5450 - $7450
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation rental Condominium in Rum Point/Cayman Kai
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Vacation rental Condominium in Rum Point/Cayman Kai

A Mid-Winter Night's Dream

This first floor unit provides easy access to the freshwater pool, white sand beach, and clear blue Caribbean.

bedrooms  2    bathrooms2
sleeps 4 - 6

$1700 - $2100
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Not Near A Beach Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation rental Villa in Rum Point/Cayman Kai
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Vacation rental Villa in Rum Point/Cayman Kai

5BR Coral Kai- Oceanfront

5BR Luxury Oceanfront Villa with Pool "Coral Kai"

bedrooms  5    bathrooms5
sleeps 10

$5450 - $7950
Per Week
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Rental Condominium in Rum Point/Cayman Kai
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Rental Condominium in Rum Point/Cayman Kai

Grand Cayman Island Beachfront Apartment

Secluded beachfront vacation apartment directly on the long white sand beach on the quiet side of the island.

bedrooms  2    bathrooms2
sleeps 4 - 6

$1540 - $1960
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
East End rental Villa
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East End rental Villa

4-7BR Cayman Castle

4-7BR Luxury Oceanfront Villa- Cayman Castle 7 Guesthouse

bedrooms  7    bathrooms7
sleeps 12 - 16

$8950 - $12450
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Villa rental in Rum Point/Cayman Kai, Grand Cayman
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Holiday Villa rental in Rum Point/Cayman Kai, Grand Cayman

4BR Villa Zara in Rum Point

4BR Super Luxury Oceanfront Villa with pool & Spa

bedrooms  4    bathrooms5
sleeps 8

$7645 - $10945
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Villa in Rum Point/Cayman Kai
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Holiday Villa in Rum Point/Cayman Kai

4BR "Heritage House" w/ Pool

4BR Oceanfront Heritage House with Pool in Rum Point

bedrooms  4    bathrooms4
sleeps 8 - 10

$5005 - $6160
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Condominium in Cayman Islands, Caribbean
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Holiday Condominium in Cayman Islands, Caribbean

Cayman Stead-Cayman Kai/Rum Point area

Beachfront Luxury condo in Grand Cayman-Sleeps 6. Snorkling, fresh water pool,Sandy,Caribbean ocean views

bedrooms  2    bathrooms2
sleeps 6 - 7

$1400 - $2200
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Villa in Northside
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Villa in Northside

4BR "Castaway Cove" in Rum Point

4BR Stunning Oceanfront views from Castaway Cove

bedrooms  4    bathrooms4
sleeps 8 - 10

$4150 - $4750
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
5 bedroom Villa in Rum Point/Cayman Kai
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5 bedroom Villa in Rum Point/Cayman Kai

Villa Bellagio Cayman

Grand Cayman Islands Villa Vacation Rental

bedrooms  5    bathrooms4
sleeps 10 - 15

$432 - $1360
Per Day
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Villa rental in Rum Point/Cayman Kai, Grand Cayman
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Holiday Villa rental in Rum Point/Cayman Kai, Grand Cayman

1BR Villa Azure in Cayman Kai

1BR Honeymoon Villa "Villa Azure" on a perfect Beach and walk to Rum Point Club!

bedrooms  1    bathrooms2
sleeps 2 - 4

$2205 - $2905
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation Villa in Breakers
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Vacation Villa in Breakers

3-4BR "Villa Cayman" with pool

4BR Luxury Oceanfront Villa with Pool and optional cottage

bedrooms  4    bathrooms3
sleeps 6 - 12

$3950 - $5484
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Villa in Rum Point/Cayman Kai, Grand Cayman
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Villa in Rum Point/Cayman Kai, Grand Cayman

5BR "Reef Romance"- Luxury Oceanfront

5BR All King Suites--Luxury Oceanfront Villa with Pool

bedrooms  5    bathrooms5
sleeps 10

$4450 - $8950
Per Week
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Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Vacation rental Villa in Little Cayman
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Vacation rental Villa in Little Cayman

Little Cayman Beach House

Tranquil Charming Secluded

bedrooms  5    bathrooms3
sleeps 10 - 12

$3000 - $6000
Per Week
Add to Shortlist
Not Near A Golf Course Pets Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Rental Condominium in Seven Mile Beach
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Rental Condominium in Seven Mile Beach

Grand Cayman Vacation Rentals

Experience Grand Cayman while staying in your own condo at any of our properties along Seven Mile Beach!

bedrooms  3    bathrooms2
sleeps 1 - 10

$205 - $750
Per Day
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Condominium for rent in Grand Cayman
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Condominium for rent in Grand Cayman

Treasure Island Condos

Rent Direct From the Owner and Save $$$
Lovely 2 Bed, 2 Bath Condo on World Famous 7 Mile Beach

bedrooms  2    bathrooms2
sleeps 4 - 6

$1505 - $2450
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
2 bedroom Condominium for rent in Grand Cayman
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2 bedroom Condominium for rent in Grand Cayman

Kaibo Yacht Club Phase 2, McKai Villa

2 bedroom, 2 bathroom luxury beachfront condominium

bedrooms  2    bathrooms2
sleeps 4 - 6

$200 - $300
Per Day
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Condominium for rent in Seven Mile Beach
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Condominium for rent in Seven Mile Beach

Grand Caymanian Resort

The Ramada Grand Caymanian Resort promises a world-class vacation in one of the world's most beautiful destinations.

bedrooms  1    bathrooms1
sleeps 2 - 4

$279 - $419
Per Day
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Rental Villa in Northside
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Rental Villa in Northside

4-5BR Cayman Sands

Oceanfront 4-5BR Cayman Sands Rental Villa with Pool

bedrooms  5    bathrooms5
sleeps 8 - 14

$5250 - $6950
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Disabled Access Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
2 bedroom Condominium in North West Point
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2 bedroom Condominium in North West Point

Kaibo Yacht Club Beach Front Condo

Enjoy the peace and tranquilty of the Rum Point/Cayman Kai beaches. Sun warms you-trade winds cool you!

bedrooms  2    bathrooms2
sleeps 4 - 6

$1365 - $1925
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Holiday Condominium in Seven Mile Beach
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Holiday Condominium in Seven Mile Beach

Tamarind Bay - Seven Mile Beahc

3 Bedroom two bath condo on the best location on Seven Mile Beach.

bedrooms  3    bathrooms2
sleeps 6 - 7

$299 - $515
Per Day
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Does Not Have Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Holiday Villa in Rum Point/Cayman Kai, Grand Cayman
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Holiday Villa in Rum Point/Cayman Kai, Grand Cayman

4BR Oceanfront "Kai Vista"

Luxury Oceanfrotn Rental Villa with Pool- "Kai Vista"

bedrooms  4    bathrooms3
sleeps 8 - 9

$5450 - $7450
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Rental Villa in Rum Point/Cayman Kai
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Rental Villa in Rum Point/Cayman Kai

4-5BR "Coconut Beach" in Rum Point

5BR oceanfront villa 'Coconut Beach" with pool in Rum Point

bedrooms  5    bathrooms4
sleeps 10

$4025 - $6950
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     

About Cayman Islands Vacation Rentals - Caribbean Holiday Rentals in Cayman Islands:

 to the Cayman Islands.

First called The Turtles ("Tortugas") by Christopher Columbus, the Cayman Islands appear to get their present name from the Carib word for a sea crocodile. What with countless turtles, crocodiles and the traditional association the Cayman Islands have with piracy, you might be forgiven for hesitating to make a holiday or vacation rental here.
But the great beaches of soft sand will ease your mind, emboldening you to dive amid coral reefs that teem with marine wildlife. You might, however, expect to meet a ghostly pirate as you explore an ancient shipwreck. Ghosts probably cannot swim, though. But you can swim with the stingray if you make holiday or vacation rentals.
Inland, the confirmed landlubber can explore dark, inviting rainforest, or maybe trek a little way along the Seven Mile Beach.
That's on Grand Cayman. But there are Cayman Brac and little Cayman to visit, too. Three splendid reasons for holiday or vacation rentals in lands once traversed by Sir Francis Drake.
There are more than three reasons for coming to the Cayman Islands: more than 100. You can find them yourself with a holiday or vacation rental.